(S)-2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid ethyl ester | 848949-91-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid ethyl ester
• 英文别名: ethyl (2S)-2-benzamido-4-fluoro-4-methylpentanoate
• CAS: 848949-91-7
• 化学式: C₁₅H₂₀FNO₃
• 分子量: 281.327
• InChiKey: GFJLODIIPFDZGX-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid ethyl ester 在 氢氟酸 作用下， 以 甲醇 为溶剂， 生成 3-Amino-5,5-dimethyl-dihydro-furan-2-one; hydrofluoride
  参考文献：
  名称：

  An Efficient Chemoenzymatic Approach to (S)-γ-Fluoroleucine Ethyl Ester

  摘要：

  An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of 2-(3-butenyl)azlactone 7b with EtOH to give amide ester (S)-6b in 84% enantiomeric excess. Removal of the N-pentenoyl group with N,N-dibromodimethylhydantoin in the presence of trifluoroacetic acid afforded the titled compound, which was isolated as its hydrogen sulfate salt in 75% yield and > 97% ee.

  DOI：

  10.1021/jo047918j
• 作为产物：
  描述：

  2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid 在 novozyme-435 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  An Efficient Chemoenzymatic Approach to (S)-γ-Fluoroleucine Ethyl Ester

  摘要：

  An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of 2-(3-butenyl)azlactone 7b with EtOH to give amide ester (S)-6b in 84% enantiomeric excess. Removal of the N-pentenoyl group with N,N-dibromodimethylhydantoin in the presence of trifluoroacetic acid afforded the titled compound, which was isolated as its hydrogen sulfate salt in 75% yield and > 97% ee.

  DOI：

  10.1021/jo047918j

文献信息

• [EN] PHOTOCHEMICAL PROCESS FOR THE FLUORINATION OF AN ORGANIC COMPOUND HAVING AN UNACTIVATED SP3 C-H BOND<br/>[FR] PROCÉDÉ PHOTOCHIMIQUE DE FLUORATION D'UN COMPOSÉ ORGANIQUE PRÉSENTANT UNE LIAISON C-H SP3 NON ACTIVÉE
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2015000076A9

  公开（公告）日：2015-08-06
• [EN] PHOTOCHEMICAL PROCESS FOR THE FLUORTNATION OF AN ORGANIC COMPOUND HAVING AN UNACTIVATED SP3 C-H BOND<br/>[FR] PROCÉDÉ PHOTOCHIMIQUE DE FLUORATION D'UN COMPOSÉ ORGANIQUE PRÉSENTANT UNE LIAISON C-H SP3 NON ACTIVÉE
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2015000076A1

  公开（公告）日：2015-01-08

  The application provides a photochemical process for the chemoselective fluorination of an organic compound by combining a carbon-containing compound having an unactivated sp3 C-H bond with a reagent system comprised of a fluorinating agent, and a photocatalyst, in the presence of a light source. Provided as fluorinating agent is N-fluorobenzenesulfonimide (NFSI) or 1-chloromethy1-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™), as photocatalyst is tetrabutylammonium decatungstate (TBADT), and as light source is a 365 nm UV lamp. The reactions conditions result in the C-H bond being replaced by a C-F bond, to provide a fluorinated carbon-containing compound.
• An Efficient Chemoenzymatic Approach to (<i>S</i>)-γ-Fluoroleucine Ethyl Ester
  作者：John Limanto、Ali Shafiee、Paul N. Devine、Veena Upadhyay、Richard A. Desmond、Bruce R. Foster、Donald R. Gauthier、Robert A. Reamer、R. P. Volante

  DOI：10.1021/jo047918j

  日期：2005.3.1

  An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of 2-(3-butenyl)azlactone 7b with EtOH to give amide ester (S)-6b in 84% enantiomeric excess. Removal of the N-pentenoyl group with N,N-dibromodimethylhydantoin in the presence of trifluoroacetic acid afforded the titled compound, which was isolated as its hydrogen sulfate salt in 75% yield and > 97% ee.